How Red Kite Went from 1 to 100 Short-Term Rental Properties: The Story So Far

We recently passed a big milestone: we now manage over 100 short-term rental homes across the Cotswolds and surrounding areas. From city flats to countryside cottages, it’s been a journey filled with lessons, last-minute callouts, and a lot of teamwork.

To mark the moment, we sat down with Freddie (Red Kite’s founder) and Sam (Project Manager and one of our early hires) to reflect on the road so far and what’s next.

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"I forgot I'd even built the website"

Freddie started Red Kite Hosts in 2021, shortly after moving to the Cotswolds from London. With a background in travel and hospitality start-ups, he saw a gap in the market for a more modern, tech-led approach to holiday let management in the area.

“I’d always wanted to start my own business. We’d moved out to the Cotswolds in 2020 and I was commuting into London a lot, which was starting to wear thin. I started looking at local holiday let management agencies and saw there was a real opportunity to do something different. So I put up a very basic website and left it there.”

The first lead came in about three months later.

“It was a Sunday morning, and honestly, I’d forgotten I even set the site live. My heart was beating. I had to quickly think through a pitch, what our service was and how we were different.”

That home became Red Kite’s first ever property, a three-bedroom house in Painswick. It was a relaxed, trusting client - ideal, Freddie says, for a first contract. “They were really understanding. I was doing everything myself back then, so it helped that they were patient as I figured everything out behind the scenes.”

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From side project to serious business

After onboarding that first home, things moved slowly. A second came a few months later, then two more in early 2022. At that point, Red Kite was still a one-man operation.

“Everything was set up and managed on Airbnb. I was running the changeovers, speaking to guests, doing listings, sending invoices, everything. The website was constantly being tweaked, and I was spending all my spare time learning SEO and Google Ads.”

Freddie's first hire was Roman, a part-time guest support assistant based in Ukraine, brought on board through Upwork shortly after the Russian invasion in early 2022.

“He didn’t have the perfect CV or the best English, but he had the right attitude and just felt like someone I could trust. When I first saw the news with Ukraine under attack, I wanted to do something useful and then this felt like a small way I could help.”

Shortly after going full-time himself, Freddie hired Liz, Red Kite’s first full-time UK team member.

“Liz came on as Housekeeping Supervisor and made it possible for me to finally hand over that whole side of the business. She was our first full-time hire and played a huge role in getting us from 10 to 30 homes. She’s still with us today as our Onboarding Lead doing a fantastic job setting up all new homes that come on board with us.”

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Scaling up: from 30 to 100 homes

When Sam joined Red Kite in January 2024, the team had grown to three: Freddie, Liz, and now Sam.

“It was just the two of them managing 30 homes, mostly through WhatsApp messages,” Sam recalls. “We had one chat for each property, with the three of us in, plus the housekeeper for that home. It worked surprisingly well, but you could see things were starting to be stretched a little. If you went for lunch, you’d come back to 20 messages across 15 chats. It was definitely time to introduce a bit more structure.”

Sam’s early role was a bit of everything: guest comms, maintenance coordination, housekeeper contact, supply orders, owner updates, hiring. As the team grew, roles became more specialised, and Sam moved into a project management role focused on all internal systems, tools and processes.

“One of the first big wins was rolling out Breezeway. We moved all of our housekeeping and maintenance task management into that system. Suddenly we had visibility, consistency, and a way to track everything in one place.”

Red Kite now uses a suite of tools to manage everything from dynamic pricing with PriceLabs, to home onboarding with a 70-point checklist system managed on Notion, to a custom-built database that stores everything from owner’s maintenance preferences, appliance make and models, hair dryer locations, housekeeper contact details, waste management information, door locking instructions, and much more.

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The Red Kite approach

While the business has grown, the core approach has stayed the same: get the details right, and make things seamless for owners, guests and housekeepers.

“We care massively about the homes we manage and the people we work with,” says Sam. “That’s always been true. What’s changed is the behind-the-scenes setup. What used to take an hour for one home might now take an hour for ten, because of the systems we’ve put in place.”

A key part of the Red Kite model is matching each property with a dedicated housekeeper - someone who knows the home, understands the owner’s preferences, and is fully supported by the ops team. But housekeeping is just one part of a much bigger picture.

“There are a lot of moving parts,” says Freddie. “We make sure all of those are covered so the owners don’t have to think about them. That’s what our full service management is all about.”

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What’s next?

With 100 homes under management, the next goal is already clear.

“We’re not aiming to be the biggest,” says Freddie… “but we do want to be the best. We want to keep improving how we operate, keep hiring brilliant people, and keep building tech that makes us more efficient. And if we get all that right, then 500 homes is the goal.”

“I’m incredibly proud of the team,” he adds. “It’s a joy to work with such a smart, creative, tenacious group of people. We’ve earned a small slice of the market through a lot of hard work and care, and we’re just getting started.”

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Do you want us to manage your home?

We offer full-service Airbnb and holiday let management across the Cotswolds and surrounding areas. Whether you own a rural retreat or a central flat, we handle everything – from listings to maintenance to housekeeping and 24/7 guest support.

👉 Get in touch here

Or if you’re interested in joining our team, we’d love to hear from you too.

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